The acquisition of Spanish-controlled Florida was a priority for American foreign policy makers during throughout the early years of the republic, especially during the presidencies of Thomas Jefferson, James Madison, and James Monroe. In 1791, Secretary of State Jefferson wrote to President Washington regarding an announcement from Spain encouraging immigrants to settle in Florida. Jefferson wished that a “hundred thousand” Americans would “accept the invitation” so that the territory would be “deliver[ed] to us peaceably” in what “otherwise [may] cost us a war.” Jefferson suggested that the administration use reverse psychology and issue a protest against “this seduction of our inhabitants just enough to make them [the Spanish] believe we think it very wise policy for them, and confirm them in it.” In 1803, President Jefferson wrote that “we shall certainly obtain the Floridas, and all in good time.” The effort to acquire Florida accelerated under President Madison. As a French diplomat remarked at the time, “the acquisition of the Floridas is the object of all of Mr. Madison’s prayers.” Madison’s State Department took the lead, using money from the Secret Service Fund that had been established by President Washington. In the summer of 1810, in West Florida (today’s Panhandle region), American settlers working in concert with the administration overthrew the weak Spanish colonial forces and immediately requested recognition from the U.S. government, which eventually absorbed the region as a U.S. territory. The government sponsored a similar operation in 1811–12 in East Florida (today’s Florida peninsula). While the operation in West Florida was conducted with quiet efficiency, the East Florida “revolt” was a fiasco. The American agent, George Mathews (1739–1812), had difficulty recruiting an indigenous force to conduct a “spontaneous uprising,” because much of East Florida was inhabited by runaway slaves and Native Americans uninterested in joining the “empire of liberty.” After his efforts to encourage an insurrection failed, Mathews recruited a paramilitary force comprised of American citizens living in Georgia who masqueraded as Floridians. Mathews eventually asked the U.S. military to intervene to support this force, at which point the covert nature of the operation was lost. As press reports proliferated and diplomatic protests from Spain escalated, President Madison decided to cancel the operation and ordered Mathews to leave East Florida. The administration denied any involvement with the effort in various exchanges with members of Congress and foreign diplomats. There are striking parallels between the operations in the Floridas and twentieth-century covert operations that also ended in disaster. The Kennedy administration, for example, attempted to topple Fidel Castro’s government by training and equipping a small force of Cuban exiles eager to overthrow the communist regime. The small force was overwhelmed when it attempted to invade at the Bay of Pigs in April 1961. Perhaps like Madison in East Florida, Kennedy underestimated the strength of the ruling government as well as the ability of the American government to keep the operation secret. Both presidents also underestimated the international repercussions that stemmed from these hostile actions. Covert operations remain attractive to presidents because of the benefits they seem to offer, but frequently these operations merely complicate matters rather than serving as a “magic bullet.” In this letter, James Madison instructed his secretary of state to alert a territorial governor regarding the “internal convulsions” that might unfold in West Florida, and to seek the governor’s help in furthering the covert action.